# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1975268'
loop_
_audit_author_name
_audit_author_address
'zhan-yong wang'
;Xinxiang University
China
;
_audit_update_record             
;
2020-01-22 deposited with the CCDC.	2020-03-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H14 O4'
_chemical_formula_weight         294.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.7002(12)
_cell_length_b                   8.4405(18)
_cell_length_c                   14.914(3)
_cell_angle_alpha                85.171(3)
_cell_angle_beta                 80.701(3)
_cell_angle_gamma                84.498(4)
_cell_volume                     703.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2011
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      27.45

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_F_000             308
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3581
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_av_R_equivalents  0.0167
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.430
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        24.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2460
_reflns_number_gt                1987
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0630P)²+0.0498P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2460
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.1137
_refine_ls_wR_factor_gt          0.1073
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2792(3) 0.3729(2) 0.56744(11) 0.0550(4) Uani 1 1 d . . . . .
H1A H 0.1324 0.4325 0.5758 0.066 Uiso 1 1 calc R U . . .
C2 C 0.4217(4) 0.3502(2) 0.63476(12) 0.0611(5) Uani 1 1 d . . . . .
H2A H 0.3700 0.3957 0.6899 0.073 Uiso 1 1 calc R U . . .
C3 C 0.6420(3) 0.2602(2) 0.62171(11) 0.0573(5) Uani 1 1 d . . . . .
H3A H 0.7341 0.2483 0.6683 0.069 Uiso 1 1 calc R U . . .
C4 C 0.7263(3) 0.18876(19) 0.54185(11) 0.0516(4) Uani 1 1 d . . . . .
H4A H 0.8725 0.1284 0.5341 0.062 Uiso 1 1 calc R U . . .
C5 C 0.5850(3) 0.20979(17) 0.47273(10) 0.0420(4) Uani 1 1 d . . . . .
C6 C 0.3657(3) 0.30286(18) 0.48724(10) 0.0444(4) Uani 1 1 d . . . . .
C7 C 0.6016(3) 0.16543(17) 0.38157(10) 0.0420(4) Uani 1 1 d . . . . .
C8 C 0.4091(3) 0.23027(17) 0.34680(10) 0.0417(4) Uani 1 1 d . . . . .
C9 C 0.3663(3) 0.21978(18) 0.25220(10) 0.0441(4) Uani 1 1 d . . . . .
H9A H 0.1982 0.2023 0.2536 0.053 Uiso 1 1 calc R U . . .
C10 C 0.5214(3) 0.06892(18) 0.21989(11) 0.0499(4) Uani 1 1 d . . . . .
H10A H 0.4321 -0.0227 0.2413 0.060 Uiso 1 1 calc R U . . .
H10B H 0.5433 0.0752 0.1539 0.060 Uiso 1 1 calc R U . . .
C11 C 0.7644(3) 0.03730(17) 0.24876(11) 0.0479(4) Uani 1 1 d . . . . .
C12 C 0.4205(2) 0.37296(17) 0.19370(9) 0.0390(4) Uani 1 1 d . . . . .
C13 C 0.6411(3) 0.39412(18) 0.14213(11) 0.0482(4) Uani 1 1 d . . . . .
H13A H 0.7597 0.3102 0.1406 0.058 Uiso 1 1 calc R U . . .
C14 C 0.6906(3) 0.53672(19) 0.09257(11) 0.0491(4) Uani 1 1 d . . . . .
H14A H 0.8412 0.5480 0.0590 0.059 Uiso 1 1 calc R U . . .
C15 C 0.5152(3) 0.66249(17) 0.09327(10) 0.0434(4) Uani 1 1 d . . . . .
C16 C 0.2938(3) 0.64389(19) 0.14460(11) 0.0506(4) Uani 1 1 d . . . . .
H16A H 0.1753 0.7279 0.1460 0.061 Uiso 1 1 calc R U . . .
C17 C 0.2476(3) 0.50160(19) 0.19367(10) 0.0474(4) Uani 1 1 d . . . . .
H17A H 0.0974 0.4911 0.2276 0.057 Uiso 1 1 calc R U . . .
C18 C 0.7716(3) 0.8326(2) -0.00585(12) 0.0620(5) Uani 1 1 d . . . . .
H18A H 0.7677 0.9382 -0.0354 0.093 Uiso 1 1 calc R U . . .
H18B H 0.8899 0.8211 0.0338 0.093 Uiso 1 1 calc R U . . .
H18C H 0.8106 0.7556 -0.0509 0.093 Uiso 1 1 calc R U . . .
O1 O 0.25527(18) 0.31549(12) 0.41047(7) 0.0474(3) Uani 1 1 d . . . . .
O2 O 0.79215(19) 0.07689(13) 0.33334(7) 0.0511(3) Uani 1 1 d . . . . .
O3 O 0.9360(2) -0.02387(15) 0.20323(8) 0.0681(4) Uani 1 1 d . . . . .
O4 O 0.5440(2) 0.80760(13) 0.04593(8) 0.0586(3) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.377(2) . ?
C1 C2 1.380(2) . ?
C1 H1A 0.9300 . ?
C2 C3 1.398(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.376(2) . ?
C3 H3A 0.9300 . ?
C4 C5 1.397(2) . ?
C4 H4A 0.9300 . ?
C5 C6 1.407(2) . ?
C5 C7 1.427(2) . ?
C6 O1 1.3850(18) . ?
C7 C8 1.339(2) . ?
C7 O2 1.3921(17) . ?
C8 O1 1.3832(17) . ?
C8 C9 1.481(2) . ?
C9 C12 1.526(2) . ?
C9 C10 1.544(2) . ?
C9 H9A 0.9800 . ?
C10 C11 1.509(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 O3 1.1968(18) . ?
C11 O2 1.3689(19) . ?
C12 C13 1.383(2) . ?
C12 C17 1.394(2) . ?
C13 C14 1.387(2) . ?
C13 H13A 0.9300 . ?
C14 C15 1.386(2) . ?
C14 H14A 0.9300 . ?
C15 O4 1.3715(18) . ?
C15 C16 1.382(2) . ?
C16 C17 1.378(2) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
C18 O4 1.423(2) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 116.57(17) . . ?
C6 C1 H1A 121.7 . . ?
C2 C1 H1A 121.7 . . ?
C1 C2 C3 121.38(16) . . ?
C1 C2 H2A 119.3 . . ?
C3 C2 H2A 119.3 . . ?
C4 C3 C2 121.84(16) . . ?
C4 C3 H3A 119.1 . . ?
C2 C3 H3A 119.1 . . ?
C3 C4 C5 117.84(16) . . ?
C3 C4 H4A 121.1 . . ?
C5 C4 H4A 121.1 . . ?
C4 C5 C6 119.10(14) . . ?
C4 C5 C7 137.20(15) . . ?
C6 C5 C7 103.65(13) . . ?
C1 C6 O1 125.74(15) . . ?
C1 C6 C5 123.27(15) . . ?
O1 C6 C5 110.99(13) . . ?
C8 C7 O2 124.51(14) . . ?
C8 C7 C5 109.17(13) . . ?
O2 C7 C5 126.21(14) . . ?
C7 C8 O1 110.85(13) . . ?
C7 C8 C9 125.68(14) . . ?
O1 C8 C9 123.43(12) . . ?
C8 C9 C12 111.42(12) . . ?
C8 C9 C10 104.46(12) . . ?
C12 C9 C10 114.81(13) . . ?
C8 C9 H9A 108.6 . . ?
C12 C9 H9A 108.6 . . ?
C10 C9 H9A 108.6 . . ?
C11 C10 C9 117.70(13) . . ?
C11 C10 H10A 107.9 . . ?
C9 C10 H10A 107.9 . . ?
C11 C10 H10B 107.9 . . ?
C9 C10 H10B 107.9 . . ?
H10A C10 H10B 107.2 . . ?
O3 C11 O2 116.96(15) . . ?
O3 C11 C10 124.36(15) . . ?
O2 C11 C10 118.66(14) . . ?
C13 C12 C17 117.11(14) . . ?
C13 C12 C9 122.67(13) . . ?
C17 C12 C9 120.16(13) . . ?
C12 C13 C14 121.94(13) . . ?
C12 C13 H13A 119.0 . . ?
C14 C13 H13A 119.0 . . ?
C15 C14 C13 119.81(15) . . ?
C15 C14 H14A 120.1 . . ?
C13 C14 H14A 120.1 . . ?
O4 C15 C16 116.24(13) . . ?
O4 C15 C14 124.63(15) . . ?
C16 C15 C14 119.13(14) . . ?
C17 C16 C15 120.33(14) . . ?
C17 C16 H16A 119.8 . . ?
C15 C16 H16A 119.8 . . ?
C16 C17 C12 121.67(15) . . ?
C16 C17 H17A 119.2 . . ?
C12 C17 H17A 119.2 . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C8 O1 C6 105.32(11) . . ?
C11 O2 C7 116.76(12) . . ?
C15 O4 C18 117.86(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.1(2) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C2 C3 C4 C5 0.5(2) . . . . ?
C3 C4 C5 C6 0.4(2) . . . . ?
C3 C4 C5 C7 177.32(16) . . . . ?
C2 C1 C6 O1 -177.66(14) . . . . ?
C2 C1 C6 C5 1.1(2) . . . . ?
C4 C5 C6 C1 -1.2(2) . . . . ?
C7 C5 C6 C1 -179.10(14) . . . . ?
C4 C5 C6 O1 177.66(13) . . . . ?
C7 C5 C6 O1 -0.18(16) . . . . ?
C4 C5 C7 C8 -176.33(17) . . . . ?
C6 C5 C7 C8 0.91(16) . . . . ?
C4 C5 C7 O2 0.2(3) . . . . ?
C6 C5 C7 O2 177.43(13) . . . . ?
O2 C7 C8 O1 -177.92(12) . . . . ?
C5 C7 C8 O1 -1.33(17) . . . . ?
O2 C7 C8 C9 -0.2(2) . . . . ?
C5 C7 C8 C9 176.35(13) . . . . ?
C7 C8 C9 C12 -101.14(17) . . . . ?
O1 C8 C9 C12 76.26(17) . . . . ?
C7 C8 C9 C10 23.4(2) . . . . ?
O1 C8 C9 C10 -159.22(13) . . . . ?
C8 C9 C10 C11 -38.92(18) . . . . ?
C12 C9 C10 C11 83.41(17) . . . . ?
C9 C10 C11 O3 -146.16(16) . . . . ?
C9 C10 C11 O2 35.5(2) . . . . ?
C8 C9 C12 C13 92.57(16) . . . . ?
C10 C9 C12 C13 -25.9(2) . . . . ?
C8 C9 C12 C17 -84.63(16) . . . . ?
C10 C9 C12 C17 156.88(13) . . . . ?
C17 C12 C13 C14 0.3(2) . . . . ?
C9 C12 C13 C14 -177.02(14) . . . . ?
C12 C13 C14 C15 -0.6(2) . . . . ?
C13 C14 C15 O4 -179.13(14) . . . . ?
C13 C14 C15 C16 0.8(2) . . . . ?
O4 C15 C16 C17 179.32(13) . . . . ?
C14 C15 C16 C17 -0.6(2) . . . . ?
C15 C16 C17 C12 0.3(2) . . . . ?
C13 C12 C17 C16 -0.1(2) . . . . ?
C9 C12 C17 C16 177.29(13) . . . . ?
C7 C8 O1 C6 1.17(16) . . . . ?
C9 C8 O1 C6 -176.57(13) . . . . ?
C1 C6 O1 C8 178.31(14) . . . . ?
C5 C6 O1 C8 -0.57(15) . . . . ?
O3 C11 O2 C7 172.31(13) . . . . ?
C10 C11 O2 C7 -9.3(2) . . . . ?
C8 C7 O2 C11 -8.7(2) . . . . ?
C5 C7 O2 C11 175.26(13) . . . . ?
C16 C15 O4 C18 178.42(14) . . . . ?
C14 C15 O4 C18 -1.6(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C16 H16A O3 0.93 2.52 3.395(2) 156.7 1_465
C16 H16A O3 0.93 2.52 3.395(2) 156.7 1_465

_refine_diff_density_max         0.116
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.045



